Organic Chemistry III

Professor Carl C. Wamser

Homework Answers, Chapter 19

Carey, pages 824 - 829

Problems 19.13 - 27 , 31 - 34

1. Give IUPAC names for the following:

a)

(1S,2R)-2-methylcyclopentanecarboxylic acid

Note - (cis) is correct but not specific enough to identify this enantiomer

b)

(E)-5-methyl-3-oxo-4-heptenoic acid

(trans) would also be acceptable

2. Write a complete mechanism for the acid-catalyzed hydrolysis of methyl acetate.
The mechanism is the exact reverse of Fischer esterification.

3. Show two different ways to prepare cyclohexanecarboxylic acid starting with cyclohexane.

The upper pathway is likely to be better because the SN2 displacement by CN- on the 2° alkyl bromide is likely to be slow and may be complicated by some elimination.